Live from Synchronization Hell

So I’m running this small strategy consultancy for the media sector (www.bergerjacobi.com) on very limited administrative support. This requires efficient self-organization, helped by all kinds of mobile and not-so mobile devices. All fine so far, if I weren’t obliged to rely on one of the biggest annoyances of the digital life called “synchronization”.

A mostly working bluetooth connection from Microsoft Entourage via Apple’s iSync (and the keyboard) kept me using my Nokia E71 for calendar and address book purposes, while the iPhone had long taken over in terms general usage. I know, both Entourage – the Mac OS equivalent of Outlook until Office for Mac 2011 came along –, and the Nokia E71 are almost anachronistic tools. But then, you should never change a winning team, shouldn’t you?

What happened is that I updated my Macbook, the command center for all my activities, to Snow Leopard in order to participate in Apple’s developer program. That brought Entourage, quite slow before that, to its knees – the program couldn’t open its own database anymore, which was supposedly intact. Time for an update to Office 2011? No, because Outlook for Mac doesn’t really sync, at least not with Mac devices. My professional life was shattered: No appointments, no invitations – and years worth of notes and to-dos apparently lost somewhere in this database that I had backed-up, but even those back-ups weren’t accessible.

To get something positive out of the situation, I decided to entirely switch to the iPhone and ditch the clumsy Nokia. Therefore, I signed up for a trial of Apple’s expensive Mobile Me service – it remained a trial, because after setting up the account several times, trying the help line and support forums, it still doesn’t sync the calendar properly. And, hey, isn’t there Google, offering this stuff for free? So I set up iCal, Mail and Address Book and connected my iPhone and iPad with Google’s Microsoft Exchange (hey, all the big guys involved!).

For a few hours, I thought I would live happily ever after. The happiness dwindled when I realized I was able to send event invitations only from my private Gmail account, not from my business account, what must look strange to long-standing clients. Then, I came across some other strange bugs. If, for example, I sent an invitation to the business e-mail of a client/colleague, Google would figure out that person’s Gmail address (previously unknown to me) and send it there instead. Annoying, no?

On the other hand, invitations sent to my business address wouldn’t open in my Google-linked iCal calendar. Also, iCal invitations didn’t show up clearly in clients’ corporate Outlook surfaces. What a mess. A few days later, after adding a random user to my Mac and going back to my own account, Entourage miraculously decided to open the database again. Back in heaven? No. It is so painfully slow and unreliable compared to Mail and iCal…

While writing this, I’m trying a solution that can only be temporary: Running iCal, Mail etc. for everything apart of invitations, which I send and receive in Entourage. This means having at least four programs permanently running on my computer (including EasyTask, an app I’m using for To Do-Lists now – it looked reasonable first, but has many bugs and doesn’t fully integrate with Snow Leopard).

Mostly, my devices sync their data somehow, but sometimes, they don’t, and in my professional context, one missing calendar entry is too much. Is there any solution to this mess? Or is it a permanent consequence of that stupid small wars the tech giants are fighting to push their platforms ahead? Don’t know. But I know that I’m frustrated. Quite a bit.

UPDATE: After the funny procedure of introducing a new user to my Macbook, then reverting to the old, some things work better. MobileMe now syncs, but in times of Dropbox et.al., I don’t really see the case for this paid solution. Also, with iCal, it shows behaviours comparable to Google Calendar – clearly not the tool of choice for business life.